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WO1998054259A1 - Composition d'elastomere contenant du fluor - Google Patents

Composition d'elastomere contenant du fluor Download PDF

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Publication number
WO1998054259A1
WO1998054259A1 PCT/JP1998/002269 JP9802269W WO9854259A1 WO 1998054259 A1 WO1998054259 A1 WO 1998054259A1 JP 9802269 W JP9802269 W JP 9802269W WO 9854259 A1 WO9854259 A1 WO 9854259A1
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WO
WIPO (PCT)
Prior art keywords
weight
polymer
fluorine
chain segment
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1998/002269
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English (en)
Japanese (ja)
Inventor
Tatsuya Morikawa
Mitsuru Kishine
Yoshihiro Shirai
Koji Matsumoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to US09/424,541 priority Critical patent/US6228943B1/en
Publication of WO1998054259A1 publication Critical patent/WO1998054259A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators

Definitions

  • the present invention relates to a fluorinated elastomer composition, and more particularly, the present invention relates to a peroxyside vulcanization-based fluorinated elastomer composition having excellent tensile properties, heat resistance, oil resistance, and the like.
  • the present invention relates to a peroxyside vulcanized fluorine-containing elastomer composition having improved moldability while having sealing properties at high temperatures.
  • fluorinated elastomers have excellent heat resistance and oil resistance, they are used in various industrial fields, such as automobiles, ships, aircraft, hydraulic equipment, general machinery, and pollution-related sectors. , O-rings, gaskets, oil seals, diaphragms, hoses, rolls, sheet materials, etc.
  • peroxide-cured fluorine-containing elastomers unlike polyol-cured and polyamine-cured, can be vulcanized even when the fluororubber has a high fluorine concentration.
  • fluororubber having iodine at the polymer terminal has an advantage that peroxyside vulcanization can be performed without blending a metal oxide.
  • peroxide vulcanized fluorinated elastomers are inferior in mold release and mold contamination during vulcanization molding, making it difficult to increase work efficiency.
  • cracks and cracks may occur, resulting in lower productivity and lower productivity.
  • non-adhesive fluorororubber composition obtained by the method of mixing the fluororubber and the fluorine-containing block polymer disclosed in Japanese Patent Application Laid-Open No. 8-1763888 achieves a certain effect.
  • the ratio of the non-elastomer component in the fluororubber-based thermoplastic elastomer used here is large, and it is not easy to mix the fluororubber and the fluorine-containing block polymer when preparing the fluororubber composition. is there.
  • An object of the present invention is to solve the problems and drawbacks of the above-mentioned peroxyside vulcanization-based fluorinated elastomer composition without impairing other excellent properties of the composition. According to the present invention, such an object is
  • a fluorinated block polymer comprising at least one elastomeric polymer single-chain segment and at least one non-elastomeric polymer chain segment, wherein the non-elastomeric polymer chain segment is 100 parts by weight of a fluorinated block polymer having a content of less than 5% by weight,
  • organic peroxide 0.05 to 10 parts by weight, preferably 0.3 to 5 parts by weight, more preferably 1 to 5 parts by weight and
  • polyfunctional co-crosslinking agent 0.1 to 10 parts by weight, preferably 0.5 to 8 parts by weight, more preferably 0.5 to 5 parts by weight
  • fluorine-containing block polymer used in the present invention include a chain composed of two or three types of polymer single-chain segments, an iodine atom present at one end of the chain, and the other end of the chain. Consists of residues from at least one iodine atom from the iodide compound present in
  • One (if the chain consists of two polymer chain segments) or two (if the chain consists of three polymer chains) of the polymer single-chain segment is (1) vinylidenefluoridonohexafluoropropylene or Pentafluoropropyrennote trafluoroethylene (molar ratio: 45 to 90: 5 to 50: 0 to 35) polymer, especially vinylidenefluoride / hexafluoropropylene / tetrafluoroethylene (molar ratio: 40 to 9) 0: 10 to 50: 0 to 30) Polymer
  • Tetrafluoroethylene Z propylene Z copolymer component for example, ethylene isobutylene, acrylic acid and its ester, methacrylic acid and its ester, vinylinolenoreolide, hexafnoreolide propylene, vinylidenefluoride de, chloro E chill ether, black hole Torifuruoroechi Ren, Pa one Furuoro (C, - C 3 alkyl Honoré vinyl ether) (molar ratio of 4 0-7 0: 3 0-6 0: 0-2 0) is selected from a polymer An elastomeric polymer chain segment having a molecular weight of 300,000 to 1,200,000,
  • Vinylidene fluoride tetrafluoroethylene (molar ratio: 0 to 100: 0 to 100) polymer, particularly vinylidene fluoride Z tetrafluoroethylene (molar ratio: 70 to 99: 1 to 30) Polymer, tetrafluoroethylene homopolymer or vinylidene fluoride homopolymer,
  • R f represents a trifluoromethyl group or a group represented by one OR f 1 (where R f 1 is a perfluoroalkyl group having 1 to 5 carbon atoms).)
  • the content of the non-elastomer polymer chain segment increases, the effect of improving the problems during vulcanization molding is increased, but the vulcanization properties are deteriorated accordingly.
  • the content of non-elastomeric polymer chain segments is less than 5% by weight, preferably less than 0.5-5% by weight, more preferably less than 0.5-3% by weight.
  • a typical structure of a fluorinated block polymer has, for example, the formula:
  • Q is a residue obtained by removing an iodine atom from an iodide compound, A, B,... Are each a polymer chain segment (at least one of which is a fluorine-containing polymer chain segment), and I is An iodine atom released from the iodide compound, and n represents the number of bonds of Q.
  • the at least two types of polymer chain segments are mutually different from the adjacent polymer chain segments (for example, those having a different structure or composition of one unit of the monomer constituting the polymer chain segments).
  • At least one is a fluorinated polymer chain segment, consisting of at least one hard segment and at least one soft segment.
  • at least one polymer single-chain segment has a molecular weight of at least 300,000 and excludes the so-called telomer region.
  • a residue obtained by removing at least an iodine atom from the iodide compound is derived from a monomer constituting the polymer chain segment or the iodide compound. Which may have some substitutions.
  • These fluorine-containing block polymers usually contain 0.0001 to 10% by weight of iodine atoms.
  • organic peroxide used in the present invention any known organic peroxide that generates a peroxy radical under vulcanization temperature conditions can be used.
  • preferred organic peroxides are di-tert-butyl peroxide, dicumyl baroxide, 2,5-dimethyl-2,5-di (benzoylperoxy) hexane, 2,5-dimethyl-2, 5—Di (t-butylperoxy) hexane and the like.
  • the content of the organic peroxide is usually 0.05 to 10 parts by weight, preferably 0.3 to 5 parts by weight, more preferably 1 to 5 parts by weight per 100 parts by weight of the fluorinated block polymer (a). Parts by weight.
  • the fluorine-containing block polymer (a) When the content of the organic peroxide is less than 0.05 part by weight, the fluorine-containing block polymer (a) is not sufficiently crosslinked, and when it exceeds 10 parts by weight, the physical properties of the vulcanized product are deteriorated.
  • the polyfunctional co-crosslinking agent used in the present invention includes a fluorine-containing elastomer.
  • Known multifunctional co-crosslinking agents used with organic peroxides in peroxyside vulcanization can be used.
  • preferred co-crosslinking agents include triaryl cyanurate, trimethallyl isocyanurate, triallyl isocyanurate, triacrylyl formal, triallyl trimellitate, N, N'-m-7-dylene bismaleate. Mid, diaryl phthalate, tetraaryl terephthalamide, tris (diarylamine) -S-triazine, triaryl phosphite, N, N-diarylacrylamide and the like.
  • the content of the polyfunctional co-crosslinking agent is usually 0.1 to 10 parts by weight, preferably 0.5 to 8 parts by weight, more preferably 100 to 100 parts by weight of the fluorine-containing block polymer (a). 0.5 to 5 parts by weight.
  • the content of the polyfunctional co-crosslinking agent is less than 0.1 part by weight, the fluorinated block polymer ( a ) is not sufficiently crosslinked, while if it exceeds 10 parts by weight, the elongation of the vulcanized product is reduced.
  • the fluorinated elastomer composition of the present invention may contain ordinary additives, such as fillers, processing aids, plasticizers, and coloring agents, which are added to the fluorinated elastomer composition as necessary.
  • ordinary additives such as fillers, processing aids, plasticizers, and coloring agents, which are added to the fluorinated elastomer composition as necessary.
  • One or more conventional vulcanizing agents or vulcanization accelerators different from (b) and (c) above may be blended.
  • a known fluororubber may be mixed as long as the effects of the present invention are not impaired.
  • the fluorinated elastomer composition of the present invention can be prepared by mixing the above-mentioned components using a usual rubber processing machine, for example, an open roll, a Banbury mixer, a humidifier or the like. it can.
  • the vulcanization of the fluorinated elastomer composition of the present invention can be carried out under ordinary vulcanization conditions for fluororubber.
  • press vulcanization is performed by placing the mold in a mold and holding it at 120 to 200 ° C. for 1 to 60 minutes under pressure. Then, when vulcanization is carried out by holding the powder in an oven at 120 to 250 ° C. for 0 to 48 hours, vulcanized rubber can be obtained.
  • VdF vinylidene fluoride
  • HFP hexafluoropropylene
  • TFE tetrafluoroethylene
  • APS ammonium persulfate.
  • ICF 2 CF 2 CF 2 CF 2 14.6 g was charged when the total amount of the additional charged gas reached 25 g, and APS 0.4 every 3 hours from the start of polymerization.
  • Weight 0 /. 10 ml of the aqueous solution was injected.
  • the solid content concentration of the produced disposable ion was 24.8% by weight.
  • the dispersion is pulverized with a line mixer having strong shearing force, and the coagulated material is washed with water and dried to obtain a Mooney viscosity of ML 1 + i.
  • a fluorinated elastomer having a temperature of 100 ° C. 50 (990 g) was obtained.
  • the inside of the tank is sufficiently replaced with pure nitrogen gas, and the tank pressure is increased to 1 kgf / cm 2 ⁇ G with TFE. 10 ml was injected. Immediately because polymerization reaction pressure drop occurs beginning, when lowered to OkgfZcm 2 ⁇ G, re pressurized to 1 kgf / cm 2 ⁇ G with TFE, an additional charge of TFE have a total 2 5 g next polymerization start When the pressure reached 1 kgf / cm 2 , the temperature was lowered and the pressure was released to stop the polymerization. The polymerization time was 2 hours and 30 minutes.
  • the polymerization time (in solid content of the obtained disperser Ji is 2 5.8% by weight, 1) 1 hour 1 0 A minutes coagulation in the same way of operation and, washed with water, obtained by drying contains Fluorine block polymer 121 viscosity ML ⁇ + i. 1 0 0. C was 95, and 1041 g of a rubber was obtained.
  • the content of PV d F segment is equivalent to 4.5% by weight.
  • the inside of the tank was sufficiently replaced with pure nitrogen gas, and then the tank pressure was increased to 1 kgfZcm 2 G with TFE, and a 0.4% by weight aqueous solution of APS 1 Oml was injected. Since immediately polymerization reaction is lower descending pressure occurs beginning, when reduced to OkgfZcm 2 G, was re-pressurized to 1 kgfZcm 2 G with TFE. This pressure drop and the additional charge of TFE were repeated, and when the additional charge of TFE reached 110 g in total, the temperature was lowered and the pressure was released to stop the polymerization. The polymerization time was 8 hours and 30 minutes. At 3 hours and 6 hours after the start of the polymerization, 10 ml of a 0.4% aqueous solution of APS was injected.
  • the inside of the tank was sufficiently replaced with pure nitrogen gas, and then the tank pressure was increased to 1 kgf / cm 2 ⁇ G with TFE to obtain 0.4% by weight of APS.
  • 1 Oml of the aqueous solution was injected. Since the polymerization reaction starts immediately and a pressure drop occurs, when O kgf / cm 2 G drops, re-pressurize with TFE to 1 kgf / cm 2 G, and the additional charged amount of TF ⁇ becomes 45 g in total.
  • the starting pressure reached 1 kgf / cm 2 G, the temperature was lowered and the pressure was released to stop the polymerization.
  • the polymerization time was 5 hours.
  • the solid content of the resulting dispersion is 25.7% by weight.
  • the Mooney viscosity of the rubber obtained by coagulation, washing and drying in the same manner as in 5) is ML + i.
  • One hundred and eighty degrees was applied at 86 to obtain 130 g of rubber.
  • the content of PTFE segment is 4.5 weight 0 /. Is equivalent to
  • the physical properties and moldability of the obtained vulcanized sheet rubber and o-ring were measured or evaluated by the following methods.
  • the moldability was evaluated by using a P-8 (65-cavity) mold for the exercise ⁇ ⁇ ⁇ ring specified in JIS- ⁇ 2401 without using an external mold release agent.
  • the press was vulcanized (1 shot: 4 minutes at 170 ° C) and evaluated on the following two points.
  • the rubber containing the compounded components is left at 40 ° C for 7 days and then press-vulcanized. This is due to the fact that triaryl isocyanurate, 2,5-dimethyl-1,2,5-di (t-butylphenol) hexane, which is a compounded component, bleeds to the surface and moldability deteriorates in summer. The state is assumed.
  • the material of the mold used was iron with hard chrome plating on the surface.
  • Example 1 Example 2 Comparative Example 1 Comparative Example 2
  • Example 3 Comparative Example 3
  • the fluorinated block copolymers of Examples 1 and 2 (vinylidene fluoride / tetrafluoroethylene / hexafluoropropylene elastomer, respectively, PTFE segment 2.5 weight 0 /.,? (1? Segment 4 (Containing 5% by weight) compared with the known peroxide-curing fluororubber (vinylidenefluoride / tetrafluoroethylene / hexafluoropropylene elastomer) of Comparative Example 1.
  • the moldability is excellent because the number of remaining O-rings is small and there is no contamination due to a part of burrs.
  • the fluorinated block polymer of Comparative Example 2 has a PTFE segment content of 10% by weight and is excellent in mold moldability, but has disadvantages such as increased vulcanizate hardness and poor compression set. This is due to the large percentage of PTFE segments.
  • Example 3 of the fluorine-containing Proc polymer (vinylidene fluoride Rai to de hexa full O b pyrene Heras Tomah foremost PTFE segment 4.5 wt 0/0 containing) known Paokisai de vulcanization fluororubber of Comparative Example 3 (vinylidene full Compared to Olive / Hexafluoropropylene Elastomer), moldability is excellent because there is no contamination by part of the glue.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition d'élastomère contenant du fluor et pouvant être vulcanisée par un peroxyde. La composition est constituée de 100 parties en poids d'un polymère séquencé contenant du fluor, qui comprend au moins un type de chaînes élastomères et au moins un type de chaînes non élastomères, et dont la teneur en chaînes non élastomères est inférieure à 50 % en poids, 0,05 à 10 parties en poids d'un peroxyde organique et 0,1 à 10 parties en poids d'un agent de coréticulation polyfonctionnel. Cette composition présente une meilleure aptitude au moulage par vulcanisation, tout en conservant d'excellentes propriétés de traction, de résistance thermique, de résistance à l'huile, d'obturation à haute température, etc., égales à celles des compositions connues d'élastomères contenant du fluor et pouvant être vulcanisées par un peroxyde.
PCT/JP1998/002269 1997-05-26 1998-05-25 Composition d'elastomere contenant du fluor Ceased WO1998054259A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US09/424,541 US6228943B1 (en) 1997-05-26 1998-05-25 Fluorine-containing elastomer composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP9/134780 1997-05-26
JP9134780A JPH10324788A (ja) 1997-05-26 1997-05-26 含フッ素エラストマー組成物

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WO1998054259A1 true WO1998054259A1 (fr) 1998-12-03

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JP (1) JPH10324788A (fr)
WO (1) WO1998054259A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1209176A4 (fr) * 1999-06-30 2002-09-18 Daikin Ind Ltd Materiau compose fluore souple, resistant a la chaleur et non collant
EP0885928B1 (fr) * 1997-06-20 2002-12-11 Ausimont S.p.A. Elastomères thermoplastiques fluorés et articles à base de celui-ci
JP2009256658A (ja) * 2008-03-28 2009-11-05 Daikin Ind Ltd 燃料低透過性ブロック共重合体

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KR20010071750A (ko) * 1998-07-17 2001-07-31 이노우에 노리유끼 불소고무 조성물
US6797149B2 (en) * 2002-04-02 2004-09-28 Intercorr Holdings, Ltd. Apparatus and method for electrochemical detection and control of inorganic scale
US6921796B2 (en) * 2002-07-29 2005-07-26 Illinois Tool Works, Inc. Fluoroelastomer compositions, their preparation, and their use
FR2849046A1 (fr) * 2002-12-24 2004-06-25 Atofina Composition a base de pvdf heterogene et de bisimide aromatique reticulable par des radiations ionisantes
US7261946B2 (en) * 2003-11-14 2007-08-28 Advanced Cardiovascular Systems, Inc. Block copolymers of acrylates and methacrylates with fluoroalkenes
US7135122B2 (en) * 2004-03-31 2006-11-14 Freudenberg-Nok General Partnership Polytetrafluoroethylene composites
US7452577B2 (en) * 2004-06-30 2008-11-18 Freudenberg-Nok General Partnership Electron beam curing of fabricated polymeric structures
US7342072B2 (en) * 2004-06-30 2008-03-11 Freudenberg-Nok General Partnership Bimodal compounds having an elastomeric moiety
US20060000801A1 (en) * 2004-06-30 2006-01-05 Park Edward H Surface bonding in halogenated polymeric components
US7230038B2 (en) * 2004-06-30 2007-06-12 Freudenberg-Nok General Partnership Branched chain fluoropolymers
US7244329B2 (en) * 2004-06-30 2007-07-17 Freudenberg-Nok General Partnership Electron beam curing in a composite having a flow resistant adhesive layer
US7521508B2 (en) 2004-06-30 2009-04-21 Freudenberg-Nok General Partnership Electron beam inter-curing of plastic and elastomer blends
US7381765B2 (en) 2004-11-08 2008-06-03 Freudenberg-Nok General Partnership Electrostatically dissipative fluoropolymers
US20060099368A1 (en) * 2004-11-08 2006-05-11 Park Edward H Fuel hose with a fluoropolymer inner layer
US20060100368A1 (en) * 2004-11-08 2006-05-11 Park Edward H Elastomer gum polymer systems
US20070048476A1 (en) * 2005-08-31 2007-03-01 Freudenberg-Nok General Partnership Assemblies sealed with multilayer composite compression seals having a layer of dispersed fluoroelastomer in thermoplastic
US20070044906A1 (en) * 2005-08-31 2007-03-01 Freudenberg-Nok General Partnership Multilayer polymeric composites having a layer of dispersed fluoroelastomer in thermoplastic
US20070045967A1 (en) * 2005-08-31 2007-03-01 Freudenberg-Nok General Partnership Assemblies sealed with multilayer composite torsion seals having a layer of dispersed fluoroelastomer in thermoplastic
US8034874B2 (en) * 2005-11-23 2011-10-11 Boston Scientific Scimed, Inc. Medical devices having polymeric regions that contain fluorocarbon-containing block copolymers
US7863365B2 (en) 2006-12-20 2011-01-04 Freudenberg-Nok General Partnership Robust magnetizable elastomeric thermoplastic blends
JP5029389B2 (ja) * 2008-01-24 2012-09-19 ダイキン工業株式会社 樹脂分散液連続凝析方法
EP2935356B1 (fr) 2012-12-19 2016-10-05 3M Innovative Properties Company Procédé de fabrication fluoropolymeres avec un polyiodures, compositions et ouvrages
EP3571235A4 (fr) * 2017-01-18 2020-11-11 3M Innovative Properties Company Copolymères à blocs fluorés dérivant de monomères à site de durcissement contenant un nitrile

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JPH08176388A (ja) * 1994-12-22 1996-07-09 Fujikura Rubber Ltd 非粘着性フッ素ゴム組成物

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JPS5386786A (en) * 1977-09-30 1978-07-31 Daikin Ind Ltd Polymer having fluoring-containing segment and production
JPH08176388A (ja) * 1994-12-22 1996-07-09 Fujikura Rubber Ltd 非粘着性フッ素ゴム組成物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0885928B1 (fr) * 1997-06-20 2002-12-11 Ausimont S.p.A. Elastomères thermoplastiques fluorés et articles à base de celui-ci
EP1209176A4 (fr) * 1999-06-30 2002-09-18 Daikin Ind Ltd Materiau compose fluore souple, resistant a la chaleur et non collant
US6706819B1 (en) 1999-06-30 2004-03-16 Daikin Industries, Ltd. Flexible fluorine-containing material having heat resistance and non-tackiness
JP2009256658A (ja) * 2008-03-28 2009-11-05 Daikin Ind Ltd 燃料低透過性ブロック共重合体

Also Published As

Publication number Publication date
JPH10324788A (ja) 1998-12-08
US6228943B1 (en) 2001-05-08

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